N-cyclopropyl-2-difluoromethoxy-3-halogenoanilines and intermediates for the preparation thereof

Abstract

N-Cyclopropyl-2-difluoromethoxy-3-halogenoanilines which serve as important intermediates in the preparation of quinolonecarboxylic acids useful as synthetic antimicrobial agents from industrially inexpensive and easily available raw materials; and intermediates for the preparation thereof. Specifically, compounds represented by the general formula (1), (2) and (3),wherein X is halogeno; and Y is nitro or amino, (2) wherein X is halogeno; and R1 is lower alkyl, (3) wherein X is halogeno; and R is hydrogen or -CH=C(CO2R2)2, R2 being lower alkyl.

What is claimed is:  
     
       1. A difluoromethoxybenzene derivative represented by the following formula (1):                    
       wherein X is a halogen atom and Y is a nitro group or an amino group.  
     
     
       2. An N-(1-alkoxycyclopropyl)-2-difluoromethoxy-3-halogenoaniline derivative represented by the following formula (2):                    
       wherein X is a halogen atom and R 1  is a lower alkyl group.  
     
     
       3. An N-cyclopropyl-2-difluoromethoxy-3-halogenoaniline derivative represented by the following formula (3):                    
       wherein X is a halogen atom and R is a hydrogen atom or a 2,2-di(alkoxycarbonyl)ethylene group represented by the following formula (4):  
       
         
           —CH═C(CO 2 R 2 ) 2   (4)  
         
       
       (wherein R 2  is a lower alkyl group).